What is Crossdressing?

I think it’s easy to overthink who we are and why we like what we like.

Why do I like heels?  Why do I wear panties?

I suppose we are a psychologist’s dream, an opportunity to examine and dissect every aspect of our lives to determine why we are who we are.

But the truth is that this is just who we are.  There’s likely no psychological reason for what we wear, just as there likely is no reason someone prefers a particular season over another.  It just is.

I absolutely think there is too much time debating and discussing gender and why someone is who they are.  We simply are who we are.  There are a lot of terms someone can identify with when it comes to gender and I think it’s wonderful there’s so many options, and at the same time I think these labels are there to make others feel comfortable with us.

“Why is that man wearing a dress?”

Because they are transgender.

“Why is that person referring to themselves as ‘they’ and not ‘he’ or she’?”

Because they are agender.

Using a label or a term can help someone put who we are in some sort of framework.  When we say we are transgender, it gives them sort of structure for them to process who we are.

“Oh, you’re transgender, like Chaz Bono or Laverne Cox.”

Well, yes, and no.  Yes, we are transgender, but we are transgender is different ways.  Some trans people take hormones and legally change their name, some happily and deliberately bounce back and forth between gender identity and presentation.

For someone who thinks that we overthink labels and gender, I sure spend a lot of time thinking about them.  I wrote about how my definition of transgender is pretty expansive and inclusive, but I started to think about what crossdressing is.

If I consider my definition of what I feel being transgender is, crossdressing falls under that umbrella.  Some in our community identify as crossdressers but not as transgender.

But what is crossdressing itself?

When I was younger I knew I liked wearing “girls clothes”, but it wasn’t until I was in grade school when my friend mentioned an episode of the Donahue show that featured crossdressers.  As someone who was raised Catholic, that term could have very well meant something religious. I asked her what that word meant and she said it was a word for men who wore girl clothes.

My world exploded.

I never thought there was anything “wrong” with me, but I knew that not many boys dreamed about wearing dresses or sneaking into their mom’s closet and trying on her high heels.  I couldn’t imagine that I was the only one like me, but to learn that there were so many others like me that there was a word for us was a life-changing moment.

I was a crossdresser.

The word, in a way, legitimized who I was.  It explained me. It defined me. It was a word I could use to describe myself.  It was a word I could use instead of telling others that I wanted to, and that I liked to wear makeup, dresses, and, well, girl clothes.  It’s hard to describe, but I suddenly felt better about myself. I wasn’t alone.

As I grew into adolescence and into my teens, I learned that the word wasn’t necessarily one that had many positive associations.  A crossdresser was a freak, an ugly portrayal of women, a pervert, a joke. A crossdresser was someone to be afraid of. Pop culture did no favors to the non-gender conforming community.  Whether it was the Tina character in ‘Funky Cold Medina’ or Bugs Bunny in drag, a boy wearing a dress was played for laughs.

I was crushed.  I was never ashamed about who I was, but instances like these made me more protective and paranoid of my secret more than ever.

The internet wasn’t much help, either.  My first day of college was in 1994 and the web was still a newish thing.  The computers in the library was my first opportunity to look up anything I wanted.  Google wasn’t a thing yet, but I looked for the term ‘crossdresser’ on my very first online search.

Pictures and stories of men wearing lingerie flooded the search results.  I panicked. The last thing I wanted on my first day of college is someone to walk by and see what I was looking at.  I logged off, more dispirited than ever.

Were crossdressers perverts?  Was I? There was never anything sexual in my dressing.  Yes, I loved, and still love lingerie, but that’s not what it was about.  What is more beautiful than a lacy bra and delicate panties paired with stockings?  Dressing was about looking and feeling beautiful. The feeling of belonging that I first felt when I learned that word had completely vanished and I felt more alone and misunderstood than ever before.  I questioned who I was and whether or not the word was right for me.

I hadn’t learned the word ‘transgender’ yet so crossdresser was the only word I knew for someone like me.  So, what were we? What is a crossdresser? This is a discussion many in our community disagree on. I fully accept that there may likely never be a term that is satisfying and universally accepted.  However, I wanted to clarify what I mean when I use this word.

Crossdressing is simply wearing clothes that are typically associated with another gender.

A boy wearing panties, a woman wearing a tie.  That’s crossdressing.

I use the word ‘typically’ with some qualifiers.  I do not think cisgender women wearing pants is considered crossdressing.  Women have been wearing pants long enough for society to accept that women are “allowed” to wear pants.  Yes, there are ties that are made for women, just as there panties that are made for the cisgender male anatomy.  I still think that my example above fits my definition as those clothing items are overwhelming associated with a specific gender.

What crossdressing does for the individual person is as unique as the person.  Someone might feel beautiful, powerful, horny, calm, happy, whatever. I do not believe a crossdresser is necessarily a pervert.  I do not believe everyone who identifies as a crossdresser is wearing what they want for a sexual reason. Yes, there are those that do, but not everyone.

A crossdresser may have a limited scope for what they enjoy wearing.  Some crossdressers may only enjoy wearing high heels or lingerie. For some it’s all about eyeliner and that’s it.  Some crossdressers will wear anything from wigs to stockings to skirts to leggings to jewelry. There’s really no right or wrong way to crossdress.  So, just like my definition of transgender is pretty far-reaching, my definition of crossdressing is just as expansive. I believe that by having an expanded perspective on this word, it makes it more socially acceptable.  It challenges the exhausting, inaccurate, and common ‘crossdressers are perverts” opinion.

Hopefully someday terms like crossdressing won’t need to exist and people can wear whatever they want without people batting an eyelash.  The hill I’ll die on is that there are no such things as boy clothes or girl clothes. They’re just… clothes.

So, what do you think?  Do I get this right or am I far off the mark?

Love, Hannah



43 thoughts on “What is Crossdressing?

  1. I think like you Hannah.
    I know very well that we are transvestites and we live it with many nuances and differences.
    But being happy and feeling ourselves is something that has no price or logical explanation.
    We feel this way … we must assume our reality.
    And we know that our life would not be complete, nor happy, if we stopped being “girls” at least for that moment.
    Life is short … and nature is wise.
    Kisses for you!! and …. ohh I forgot ….. you look beautiful !!!


    1. I’m in the closet but more and more people are finding out. I mean sure I’m embarrassed more for them than myself. Totally agree we need a world where they “are” just clothes. Awww the freedom I can only imagine. Love your column. Any advice where u can find some like minded people on line without costing cash?


  2. For years, there was a sexual aspect to my dressing, and I never wore makeup or a wig. But from the neck down, I was all girl, and always in a dress and heels. However, now I will wear jeans, flats, makeup, and my wig because I am going out, with no sexual feelings at all. So I agree that the word “crossdresser” may mean different things to many people, with your definition showing a wider sense of understanding.


  3. Hannah, you always put a lot of thought into what you write and I think you’re spot on. I am also “A boy wearing panties”.
    I love to travel to Europe and I have always thought that cross dressing is a lot like traveling somewhere new and exciting. I enjoy being a gurl and would regret never exploring my feminine side, because that’s who I am.


  4. Hi Hannah, like most of our ilk I have spent too much time thinking and reading about why I am as I am.
    I think we are brought up by society to be boys or girls who go on to fit the social model in most cases appropriately. And maybe there is a biological component to parts of these imposed models.
    But there are some particular things that a particular boy or girl will find does not fit well with them. Some boys hate sport or woodworking. Some girls hate cooking or makeup. And society accepts that. It may even applaud such behaviour as someone being who they realise they really are. “Everyone is unique”.
    Others find that the gender fit is more difficult to accept if it defines who should and should not feel beautiful, caring, vulnerable, powerful, courageous and on and on. They go more to the heart of society’s gender construct. They are therefore more rigidly enforced.
    If we look at society’s gender expectations we can see clearly what will be accepted and what won’t.
    I didn’t realise until age 60, that I was a crossdresser and therefore somewhere on the transgender spectrum; that here was a vehicle that allowed me in my own mind to assume feelings and values for me that would generally be accepted as feminine qualities.
    I believe that dressing is a flag or symbol of gender traits that are forbidden to the opposite gender and by accepting that flag we are able to accept those traits we realise we need to accept and exhibit.
    Crossdressing even so late in my life suddenly made sense of a lot of things I had never understood or been able to accept in me.
    I think it enabled me to go beyond the very strict and limiting male model I had until then accepted blindly as ME. I could accept difference in other men and women but not in me.
    So clothes and makeup are now important to me but more importantly they are a flag that allows me to accept a broader range of qualities in me.
    This is difficult for me to fully grasp. No wonder those who have no need to dress have no idea.


  5. I’m so glad somebody else mentioned that Donahue episode. It was such a feeling of hope that I could find somebody else out there who liked to crossdress. Although I felt more normal after watching it, I turned the channel once I thought my Mom was entering the room. Crossdressing was still more of a a societal joke back then as you mentioned Hannah. I was pretty sure she wouldn’t have judged me but I didn’t want to chance it. In the youtube video of this Donahue / Tri ess episode you can see the whole range of society’s reactions from the audience from applauding the panelists to being disgusted by them. It’s great to see these pioneers in a way.


  6. I enjoy your writing, Hannah – keep on keeping on (that phrase may date me, for those old enough to remember). I believe my own personal realization of just how alone I wasn’t was in the late 90’s, when I did an internet image search for “treasure chest”. One of the pictures was a woman sitting on a pirate chest. I looked, and looked again – was that really a woman? I went to the site, and found Helen Millen’s Flickr page – lots of pictures (all tasteful!) of Helen out and about with a whole raft of friends and lots of comments from others, pretty much all of whom identified as t-girls. What an inspiration for someone like me – it opened up a whole new world!


  7. Things stopped at New Year but when I was crossdressing, I was one of those people who just wore lingerie – nothing further. It was sexual at times, yet other times, it wasn’t. It was merely lovely, comforting, cosseting, enveloping, sensual, relaxing – I’m sure I could come up with many more superlatives.

    But the very word is, and seemingly is always destined to be stereotypeed, in fact, anything remotely connected will be similarly so, subjected to ignorant slurs, side-swipes, derogatory tones etc.

    One of my blog entries of yesteryear, I think, sought an alternative descriptor, but struggled in vain to find one, so had to accept the best fit – that of doing what it says on the proverbial tin – a person deemed of one societal gender, wearing clothes of another.

    My blog (not that I’m intending to plug it by the way) has also repeatedly asked why it is OK for females to wear certain garments usually associated with men – for example, a woman can wear a suit or trousers, yet societally, it is in no way acceptable for a man to wear a skirt, except when it is a kilt, which is somehow seen differently despite the similarities in garments – tradition more than permitting it.

    In short, there is a very long way to go. Frustrating eh?

    A great and thought provoking post nevertheless Hannah – thank you.

    F. x

    Liked by 1 person

  8. Another wonderful post. Speaking of dating myself, I was intrigued by the numerous shows by Sally Jesse Raphael. But when you really trace it back, I believe most of the social stigma and negativity towards our community, past and present, can be placed at the feet medical field. Psychiatric field to be exact. Who first labeled us as having mental disphoria, Sigmund Freud? Even the ones that supposedly support trans people still push that label. Psychiatric and Sociology doctors aren’t about to let go of that money tree. I’ve never thought of myself and as most of you as having disphoria or being mental ill. This is what society has been taught forever. It’s a wonder we’ve come this far. Mostly due to people like Hannah.


  9. This was a great read. Thank you Hannah. I’m new to the world of crossdressing. My husband recently confided in me (FINALLY) and he struggles with conveying his feeling s about it. Thank you for this.

    Liked by 1 person

    1. Thank you! I read your blog and I hope you and your spouse find other writings of mine helpful. I know it’s not easy to be married to a girl like us.

      Love, Hannah


  10. So many thoughts have been passing through my mind lately and it gets a bit overwhelming. It started with just pantyhose many years ago and has grown slightly. I bought my very first pair of heels recently and also painted my toes for the first time. Which I might add is a delight to look down and see how pretty they are. It is a bit confusing because yes it is a sexual response a lot, but not always. Sometimes I just like having a skirt and hose on just to lounge in, just to feel feminine and pretty. I will most likely never be fully open about it but at some point I would like to be able to go out somewhere safe. It’s an exciting and scary time. As far as identifying I haven’t even thought of that, I’m still the same man as I was, I just like to dress up now and then. It’s nice to read others thoughts on this as I make this journey myself. Thank you!


  11. Thank you once more for your direct commentary and wide open mind. I’m personally sure that “transvestite” is usually a pejorative term, while “crossdresser” is a little less loaded, “Fetish” also has an edge; somehow it’s implied that getting exquisite sexual pleasure from dressing up is somehow bad. A pox on all the houses! Anything that you do that is so comically innocent, that sends tons of oxytocin flooding into your blood, just like being touched or stroked by another person, or petting a beloved pet, that gives you that warm flowing pleasant rush that I felt around age 9 or 10 in a white bra and a taffeta hot pink petticoat , [and nylon panties of course], in this crazy isolated separated angry world which we in- habit becomes a source of peace, calm, concrete pleasure, and place to rest, like a base camp on the path up the mountain of life. Like Hannah, I can go in and out of being a pretty woman of authenticity or a man, equally honestly, and with self respect and compassion for myself and most other people, and I do find a little estradiol from time to time to be kind and good to both the guy and the gal that coinhabit my soul. It is hard to explain to those who never question the status quo. Keep sharing Hannah and I’ll keep listening, sitting here made up in a pretty silk party dress.


  12. cross dressing is that men wear female cloths and woman wear men clothing, that is x dressing, some one who wears the opposite clothing of who there are. so why do woman wear manly cloths and that is not x dressing or some one saying to them about that is for men tow wear not woman. but when men wear a dress or bar or nylons or just x dress from head to toe. let them its who we are and showing our fem side just like woman showing off their manly side. no days real woman do not dress like woman, they wear pants and shirt, no make up, no perfume, no ear rings or heels, sneakers, socks. and that’s OK with them. so why can not us men wear female clothing? its just clothing to cover up our body. who cares what people wear now days and if you see a man wearing a dress don’t say nothing to them just keep walking, or maybe whistle at her and walk, that would tell that person she looks pretty


  13. Hannah once again your words are spot on. When it comes to what we are I like everything you say, but as a straight man I struggle to call myself transgender. I am not attracted to men nor do am I seeking the attention of a man. I love women I love all aspects of women. Including their fashion. But as a logical person I fully understand with your logic in the fact that as males we are doing a gender bend. Thus we fall into the transgender spectrum. Please keep sharing your thoughts. I found your site yesterday and I have read just about all you have wrote. I am trying to find stuff to help me with my wife and her understanding of what we do.

    Liked by 1 person

    1. Hi! Just remember that being transgender has nothing to do with you are attracted to. Gender identity and sexual identity are completely unrelated.

      Love, Hannah


  14. what is cross dressing! it is wearing the opposite clothing of a person, male or female. it’s not transgender or anything like that. we see woman wear men clothing on a daily basis and that is ok we just walk on by and say nothing, but when men wear a skirt or dress or just shorts with tights on, we get called names! what is up with that???? society needs to wake up and let us cross dress and let us be who we want to be and dress up. We just like to dress up and look pretty and go on our business, there is more men wearing female clothing then woman think, and society knows of. sorry if i am wrong but leave men alone on dressing up let them be happy and free and most likely helps them relax and be depressed free


  15. thank you, Hanna, for the words of wisdom and all what you have posted, hope people will read this and realize what is cross dressing?


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